Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...

S. Arrasate Doktorego-Tesia
CH O
3
N
H
CH
3
Etekina: %88.
[α]D 20 : +33.2 (c = 0.3, CHCl3) 12
P.f.: olioa.
es: %32 (Chiralcel OD, hexano/2-propanol %20, 0.8 mL/min, tr (S) = 7.3 min (%33.8);
tr (R) = 7.7 min (%66.2).
1 H-NMR (δ, ppm): 1.48 (d, J = 6.7 Hz, 3H, CHCH3), 1.98 (s, 3H,COCH3), 5.09-5.15
(m, 1H, CHCH3), 5.76 (sa, 1H, NH), 7.27-7.32 (m, 5H, Harom).
13 C-NMR (δ, ppm): 21.6 (COCH3), 23.5 (CHCH3), 48.7 (CHCH3), 126.1, 127.4, 128.6
(Carom-H), 143.0, (CaromC), 169.0 (CO).
IR (CHCl3): 3280 (N-H), 1639 (C=O), 1278 (C-N) cm -1 .
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 164 (M +1 , 6), 163 (M + ,55), 149 (7), 148 (27),
120 (24), 107 (10), 106 (100), 105 (18), 104 (36), 103 (8), 83 (9), 79 (15), 78 (7), 77
(14).
5.4.2. 23 N-(1-fenilpentil)sukzinimidaren sintesia.
Azido azetikotan (10 mL) egindako butilbentzilaminaren (167 mg, 1.0 mmol)
disoluzioari [(R)-2b-ren hidrolisitik datorrena], anhidrido sukzinikoa (184 mg 1.8
mmol) gehitu zitzaion, erreakzio-nahastea 16 orduz birfluxuan mantendu zelarik.
Ondoren disolbatzailea hutsean lurrundu zen 23 produktua olio modura lortu zelarik
(240 mg, 0.98 mmol).
12 a) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. Engl. 2002, 41, 1612. b) Dahmen, S.; Braese, S. J. Am.
Chem. Soc. 2002, 124, 5940. c) Lee, S.-G.; Zhang, Y.-J.; Song, C.-E.; Lee, J.-K.; Choi, J.-H. Angew.
Chem., Int. Ed. Engl. 2002, 41, 847. d) Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J. J. Chem. Soc.,
Perkin Trans 1 2002, 2, 257. e) Choi, Y. K.; Kim, M. J.; Ahn, Y.; Kim, M.-J. Org. Letters 2001, 3, 4099.
f) Maezaki, N.; Furusawa, A.; Uchida, S.; Tanaka, T. Tetrahedron 2001, 57, 9309.
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